Dependence of the decomposition rate of furoxanes on the polarity of the solvent

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Abstract

The decomposition rates of diphenylfuroxane and a number of 4-nitro-3-alkyl-furoxanes in dilute solutions were measured by manometric and calorimetric methods. In no case, an increase in the reaction rate was detected with an increase in the polarity of the solvent, which corresponds to the absence of an increase in the dipole moment of the molecule during the formation of a transition state. Based on this result, a conclusion is made about the biradical mechanism of decomposition of uncondensed disubstituted furoxanes in solutions.

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About the authors

G. M. Nazin

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Russian Federation, Chernogolovka

A. I. Kazakov

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: akazakov@icp.ac.ru
Russian Federation, Chernogolovka

A. V. Nabatova

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Russian Federation, Chernogolovka

L. L. Fershtat

Zelinsky Institute of Organic Chemistry, the Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Russian Federation, Moscow

A. A. Larin

Zelinsky Institute of Organic Chemistry, the Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Russian Federation, Moscow

References

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2. Molecular formula

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3. Fig. 1. Kinetic curves of the decomposition reaction of compound 1 at 234.6 °C in NB (1) and DF (2), and at 200 °C in NB (3) and DF (4).

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4. Fig. 2. Kinetic curves of decomposition of compounds 2g in DF (1) and NB (4), 2a in DF (2), in the melt (3) and in NB (5) at 200 °C.

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